Something like 5-7 years ago I was, I think, a lot more awkward and less attractive, but I would often find myself sleeping with people on the first or second date.

Right now I get a lot more matches, conversations (more than I can handle) and dates, but they all go nowhere. In most cases I just don’t feel attracted; in some cases, I feel a lot of interest, but it’s usually more like curiosity, respect, conversational rapport, than butterflies. So I just keep the conversation interesting, but don’t make physical moves. None of 20+ dates since my last relationship have gotten past date 2 (I want a second date maybe once in 3 first dates, and most of them reject me; where a 2nd date happened, all chemistry from date 1 had evaporated on both ends).

I’m not sure what changed on my end, honestly, but it feels like I’ve gotten more cautious/distrustful – I think previously I would sometimes make a move even though I wasn’t feeling butterflies, kinda cause you’re supposed to. Or maybe I had butterflies more often. Or maybe I held a more optimistic view of the people I meet and thought “have sex and the rest will follow”. And it was working alright.

But now, e.g. wrapping my arm around somebody I don’t yet feel that interested in, or offering a kiss, or even making an appearance compliment, feels disingenuous.

I guess I’m just curious how other guys do this? Do you get flirty and initiate touch etc. only if you really want to / if you actually feel some kind of butterflies – or do you do it as a way of building your own attraction too? I’m trying to figure out if I’m simply not attracted enough to these people, or my sexuality has changed in the direction of “demisexual” – or whether I’m simply ruining it by being too serious until I get to know them, leaving them with a feeling of “no chemistry”.

12 comments
  1. Just chiming in to say that I have basically the same issue.

    Doesn’t matter how attractive the date is, I rarely compliment, sometimes I think the compliment, and it sounds too direct to me so I say nothing. And I know how to drop non-creepy compliments and do so regularly at work all of the time to coworkers, my kids, random service people, etc. I had a waitress compliment my date 3/4 times during a meal.

    And physical stuff I overthink. Do nothing because I feel like it’ll be awkward. Most of mine where I want a second date are one and done. Pretty sure it’s the lack of flirting.

  2. I dunno. All women are beautiful, so it’s an easy compliment to give, right? I think if you’re dating with a purpose in mind then maybe you aren’t doing anything wrong at all, you’re just looking for the right one and that takes work, but maybe consider whether being in our 30s just makes butterflies a bit less intense than they used to be?

  3. Perhaps you’ve turned into the more slow-burn type as you’ve aged? I actually respect that a lot more than guys who make moves on women who are virtually strangers to them. Something about swapping bodily fluids with someone I barely know just…no thanks. I think the right person will probably match your pace and you two will decide together when it’s time to move things along physically. Or someone will cave in to their hormones and make the first move haha.

  4. Were you using dating apps a long time ago? Apps are like going on blind dates. Often I don’t feel a connection and don’t make a move since I don’t really want to see the person again. This didn’t happen often when I was younger and meeting people entirely in person. You start to build a little bit of a connection in person prior to the date. App dates don’t have that. I’m also a bit more pickier in my 30s since I am looking for something long lasting where that wasn’t a huge concern in my 20s.

  5. I think it isn’t change/distrustful, but more majurity. Dating now has more implications than it did in the twenties, so there may be a little more pressure you put on yourself (because after 10 years of dating you can get a little skittish)

    Sex rarely comes first before attraction/butterflies. In fact some say great sex is a byproduct of a healthy relationship. If you are dating just for sex, it would make sense why you don’t feel any excitement for your partners.

    I think men need to start dating women they are genuinely interested in personality wise, and let the great sex and intimacy come from that.

  6. I’m rather awkwardly a virgin at 39. I was never properly socialized and never grew comfortable with expressing interest. My family and friends circle also disintegrated over the years. So now I’m just a random loner guy when I’m not at my job. I just don’t feel right. I can’t even imagine escalating physical intimacy. And what do I even do about it at this age? I get the biggest case of imposter syndrome even being around people discussing sexual topics.

  7. “Butterflies” aside, sounds like you don’t want to have sex with these people? It’s pretty normal to not feel comfortable making moves when that’s the case.

    Either date people that are sexually attractive to you, or figure out what’s causing you to not feel this desire. Are you really over your ex, for example?

  8. I think much of what you said is quite similar to my then vs. now experiences as well. The older I get the more I feel a kind of “It’s either ‘hell yes’ or ‘no'” kind of approach to dating and many things in life. But feeling that kind of “hell yes” about someone is pretty tough for me because it requires a certain amount of “letting go”.

    When I do go on dates 2+ or “connect” with a woman I think it’s because of successfully having “let go” enough to spark a connection. I know this is super difficult and I still struggle with doing it “at will” so to speak. Sometimes I don’t “let go” enough to make dates feel a connection with me or I only “let go” on date 1 and not on date 2, etc.

    Ultimately, I’ve concluded that people don’t just “connect” with strangers so easily, but if one person puts themselves out there it can motivate trust and connection. I make a conscious effort to be that “initiator” whenever possible these days.

  9. 30 is way different than 23, both in terms of who are you and who you are matching with. Also how women approach dating in general has changed significantly the last 5 years due to influencers, tiktok, etc.

    I can imagine as two 25 year olds, the best form of connection was just making out like mad. Compare that guy to the you today who probably (hopefully) has grown in terms of new goals, interests, etc.

  10. Comments that count as compliments?
    Your eyes sparkle when you laugh.
    You nailed your whole look tonight, so put together.
    Our strides match we must be in sync. (Obviously when walking together)
    Your work (insert job) reminds me of a movie, I loved watching it, have you seen it. (Bonus Segway out of weird topics)
    When in doubt ask her opinion about something about you Such as:
    I tried this new cologne can you smell it? Is it to flowery/musky/woodsy? (Make sure you put some on your sleeve cuff for this extend sleeve to allow her to smell. This also works for over shoulder holding bc the scent is right there side note that’s not the time to ask)
    Would I be able to fish for a compliment/critique? I got these new shoes/sneakers/footwear and think matched it to my favorite suit/dress shirt really well do you think so too? Could I have done better?

    I don’t tend to see or hear these things in office banter. Best of luck!

  11. It sounds like you’re discovering dating in your 30’s.

    It’s a common mentality and growth curve in the 20’s to start with hormones/sex/lust first and believe everything else will fall in place. Through our lived experiences we learn that that’s not how relationships last. Successful relationships take work, and we learn there are a lot of people we are not compatible with.

    We could call this being guarded, less optimistic, etc … I view this as being more respectful for our own time, energy, and boundaries.

    When the honeymoon period is over, what it takes to maintain a successful long term relationship IS curiosity, respect, good conversation. It sounds like you’re getting ready internally for that.

    We’re also all getting back into the hang of socializing. Treat this as a time you’re getting to know your new self. What served us well in the past may not be what serves us best now.

  12. You’ve just become more preoccupied with the responsibilities of life and driving your way forward to build something better. Maybe dating took a backseat to that.

    Don’t be in a rush to feel something for someone. If you believe they’re genuinely amazing, the feelings will come naturally.

    Basically, it’s not something you should worry about. I have a question though. Did you experience an intense heartbreak?

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